For the connection timed out either means the server is not listening on 
that port (5986) or a firewall is in the way.

The bad handshake might mean the server doesn't support a TLS protocol or 
cipher suite the client supports. On older Windows hosts (pre 2016) there 
is a limited set of cipher suites that they support and some more modern 
Linux clients disable these ciphers for security purposes. This is 
unfortunately a harder problem to solve but using `openssl s_client 
-connect host:5986` is a good way to test SSL problems outside of Ansible.

Thanks

Jordan
On Friday, October 7, 2022 at 4:44:48 AM UTC+10 [email protected] wrote:

>
>
> Hi Team,
>
> I need help to resolve the errors below to communicate with WinRM via 
> Ansible. What will the cause for this error?
>
> server 1-
> kerberos: HTTPSConnectionPool(host='10.x.x.x'; port=5986): Max retries 
> exceeded with url: /wsman (Caused by 
> ConnectTimeoutError(<urllib3.connection.VerifiedHTTPSConnection object at 
> 0x7f3d45abe5d0>; 'Connection to 10.x.x.x. timed out. (connect timeout=30)'))
>
> server 2-
> kerberos: HTTPSConnectionPool(host='192.x.x.x'; port=5986): Max retries 
> exceeded with url: /wsman (Caused by SSLError(SSLError("bad handshake: 
> SysCallError(104; 'ECONNRESET')";);))
>
>
> Note -HTTPS port 5986 is enabled on both servers.
>

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